title: Supramolecular photocyclodimerization of 2-hydroxyanthracene with a chiral hydrogen-bonding template, cyclodextrin and serum albumin.
abstract: 2-Hydroxyanthracene (HA) in its neutral form smoothly photocyclodimerized to four stereoisomeric [4 + 4]-cyclodimers, which were isolated and characterized for the first time, whereas the anionic form of HA turned out to be photochemically inert. Enantiodifferentiating photocyclodimerization of HA in the presence of a chiral hydrogen-bonding template (TKS159), γ-cyclodextrin (γ-CDx) and bovine serum albumin (BSA) was examined to afford chiral syn-head-to-tail and anti-head-to-head cyclodimers in modest enantiomeric excesses with TKS159 and γ-CDx, but practically no photocyclodimerization proceeded in the presence of BSA probably due to the ionization of HA in the binding sites.
authors.affiliation: Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. inoue@chem.eng.osaka-u.ac.jp.
authors.forename: Gaku
authors.initials: G
authors.lastname: Fukuhara
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Umehara
authors.forename: Saki
authors.initials: S
authors.lastname: Higashino
authors.forename: Masaki
authors.initials: M
authors.lastname: Nishijima
authors.forename: Cheng
authors.initials: C
authors.lastname: Yang
authors.forename: Tadashi
authors.initials: T
authors.lastname: Mori
authors.forename: Takehiko
authors.initials: T
authors.lastname: Wada
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Inoue
mesh_terms: D000818:Animals; D000873:Anthracenes / Q000737:chemistry*; D002417:Cattle; D003500:Cyclization; D006860:Hydrogen Bonding; D062385:Hydroxybenzoates / Q000737:chemistry; D055668:Photochemical Processes; D011759:Pyrrolidines / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D062385:Hydroxybenzoates; D011759:Pyrrolidines; C098494:TKS 159; D047408:gamma-Cyclodextrins; D012710:Serum Albumin, Bovine; C034020:anthracene; C017616:phenolic acid